Acetone imine

Acetone imine
Full structural formula of acetone imine with dimensions	Skeletal formula of acetone imine
Ball-and-stick model of acetone imine	Space-filling model of acetone imine
Names
	Preferred IUPAC name Propan-2-imine
	Other names Acetone imine; 2-Propanimine;
Identifiers
CAS Number	38697-07-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	125534 ;
MeSH	Imine Acetone Imine
PubChem CID	142304;
CompTox Dashboard (EPA)	DTXSID50191992 ;
	InChI InChI=1S/C3H7N/c1-3(2)4/h4H,1-2H3 Key: XDAGXZXKTKRFMT-UHFFFAOYSA-N;
	SMILES CC(=N)C;
Properties
Chemical formula	C3H7N
Molar mass	57.096 g·mol−1
Appearance	colorless liquid
Density	0.8 g cm−3 (25 °C)
Boiling point	57–59 °C (135–138 °F; 330–332 K)
log P	-0.56
Refractive index (nD)	1.394
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H319, H336
Precautionary statements	P210, P261, P305+P351+P338
NFPA 704 (fire diamond)	0 3 0 W
Flash point	14.7 °C (58.5 °F; 287.8 K)
Related compounds
Related compounds	Acetone oxime
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula (CH₃)₂CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimine. This compound is mainly of academic interest.

Synthesis and reactions

Acetone imine is prepared by dehydrocyanation of the cyanoamine of acetone, which is prepared from acetone cyanohydrin. Dicyclohexylcarbodiimide (CyN=C=NCy) serves as the scavenger for hydrogen cyanide:^[2]

(CH₃)₂C(NH₂)CN + CyN=C=NCy → (CH₃)₂CNH + CyN(H)-C(CN)=NCy

Upon standing at room temperature, samples of acetone imine degrade to give this heterocycle, called acetonin.

The compound hydrolyzes readily:

(CH₃)₂CNH + H₂O → (CH₃)₂CO + NH₃

This reactivity is characteristic of imines derived from ammonia. Methylene imine (CH₂=NH) is also highly reactive, condensing to hexamethylenetetramine. Upon standing, acetone imine undergoes further condensation to give the tetrahydropyrimidine called acetonin, with loss of ammonia.^[3]

The imine of hexafluoroacetone, ((CF₃)₂C=NH) is by contrast robust.^[4]

References

^ "Synonyms". Pubchem.
^ K. Findeisen; H. Heitzer; K. Dehnicke (1981). "Neue Methode zur Herstellung von Aldiminen und Ketiminen". Synthesis. 1981 (9): 702–704. doi:10.1055/s-1981-29566. S2CID 98811861.
^ Matter, E. (1947). "Über ein neues Reaktionsprodukt aus Aceton und Ammoniak (Acetonin) (A new reaction product from acetone and ammonia (acetonine)) I". Helvetica Chimica Acta. 30: 1114–23. doi:10.1002/hlca.19470300503.
^ W. J. Middleton, H. D. Carlson (1970). "Hexafluoroacetone Imine". Org. Syntheses. 50: 81–3. doi:10.15227/orgsyn.050.0081..

[1] "Synonyms". Pubchem.

[2] K. Findeisen; H. Heitzer; K. Dehnicke (1981). "Neue Methode zur Herstellung von Aldiminen und Ketiminen". Synthesis. 1981 (9): 702–704. doi:10.1055/s-1981-29566. S2CID 98811861.

[3] Matter, E. (1947). "Über ein neues Reaktionsprodukt aus Aceton und Ammoniak (Acetonin) (A new reaction product from acetone and ammonia (acetonine)) I". Helvetica Chimica Acta. 30: 1114–23. doi:10.1002/hlca.19470300503.

[4] W. J. Middleton, H. D. Carlson (1970). "Hexafluoroacetone Imine". Org. Syntheses. 50: 81–3. doi:10.15227/orgsyn.050.0081..

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